5-Fluoro-2-nitroaniline → HCID 178453965, compound

HRID 1024806Notes

Reaction equation

[C:1]([O:5][C:6](=[O:33])[NH:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([C:14](=[O:32])[NH:15][C:16]2[CH:21]=[C:20]([OH:22])[CH:19]=[C:18]([O:23][C:24]3[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][CH:25]=3)[CH:17]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].F[C:35]1[CH:36]=[CH:37][C:38]([N+:42]([O-:44])=[O:43])=[C:39]([NH2:41])[CH:40]=1>>[C:1]([O:5][C:6](=[O:33])[NH:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([C:14](=[O:32])[NH:15][C:16]2[CH:17]=[C:18]([O:23][C:24]3[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][CH:25]=3)[CH:19]=[C:20]([O:22][C:35]3[CH:36]=[CH:37][C:38]([N+:42]([O-:44])=[O:43])=[C:39]([NH2:41])[CH:40]=3)[CH:21]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

Reactant 2

HCID 753995-Fluoro-2-nitroaniline

HCID 178453966HCID 178453966, compound

Product 1

HCID 178453965HCID 178453965, compoundYield 51.5%

Procedure

Using {trans-4-[3-(4-cyano-phenoxy)-5-hydroxy-phenylcarbamoyl]-cyclohexyl}-carbamic acid tert-butyl ester (1.5 g, 5.29 mmol) and 5-fluoro-2-nitro-phenylamine (0.91 g, 5.82 mmol) following the procedure of Example 42(b) afforded 1.6 g of the required product 1H NMR (DMSO-d6): δ 1.45 (9H, s), 1.8 (4H, m), 2.5 (4H, m), 3.2 (1H, m), 6.48 (2H, m), 6.75 (1H, d), 7.24 (2H, m), 7.51 (4H, m), 7.78 (2H, d), 8.05 (1H, d), 8.38 (1H, d).

Sources & evidence

ORD record: ord-e86f9d8970144da6ac1da630b00655f2
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722930B2

Reaction notes

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